It was on December 28, 2008, soon after Israel launched its punishing military campaign in Gaza, known as Operation Cast Lead, that Rabbi Brant Rosen hit the “send” key for a blog post that he believed could well pitch him out of his pulpit.

“We good liberal Jews are ready to protest oppression and human-rights abuse anywhere in the world, but are all too willing to give Israel a pass,” Rosen had typed out as Israel’s bombs were falling on Gaza — part of a massive response, with numerous civilian casualties, to rockets fired into Southern Israel by the Palestinian faction Hamas, which controls the territory.

“What Israel has been doing to the people of Gaza,” Rosen wrote on his blog, Shalom Rav, “is an outrage.”

Rosen, then a decade into his tenure as spiritual leader of Jewish Reconstructionist Congregation, a 520-household synagogue in Evanston, Ill., concluded his 221-word post with these sentences: “There, I’ve said it. Now what do I do?”

That rhetorical question came from a writer whom Newsweek had named earlier that year to its list of the top 50 pulpit rabbis in the United States.

Today, Rosen, 50, heads the rabbinical council of a group called Jewish Voice for Peace, which makes him a high-profile official with an organization on a much different kind of list: the Anti-Defamation League’s “Top Ten Anti-Israel Groups in the U.S.” for 2013.

JVP, which is No. 6 on the list, does not just criticize Israel’s fundamental policies toward the Palestinians and Iran, while claiming its position as a matter of Jewish values. The group contains a range of Israel critics, from self-described left-wing Zionists who favor some form of binational state to anti-Zionists. And it supports boycott, divestment and sanction campaigns against targets it views as involved in Israel’s occupation of the West Bank. As an organization, it is determinedly agnostic on whether Israel should be governed as an explicitly Jewish state.

Image: aaron cahan

No to Occupation: Rabbi Brant Rosen speaks last month at a Palestinian popular demonstration against the Israeli separation wall in the West Bank village of Al Ma?asara.

That represents a long journey for Rosen, whose decision to become a rabbi still surprises even him.

“I was not the worst in Hebrew school, but I was part of that pack,” the Los Angeles native said. “Our class was legendary in high school for chewing rabbis and teachers up and spitting them out.”

Rosen later connected with his Jewish identity in college, he said, when he fell in with “Habonim types,” referring to the Labor Zionist youth group. He soon came to identify as a “left-wing, progressive Zionist.” But when he ultimately turned toward making Judaism the central focus of his life, and enrolled in rabbinical school, he “swore up and down” that he’d never become a congregational rabbi.

Rosen basically agreed with a classmate who told him she wouldn’t pursue a pulpit because she didn’t want to “help comfortable middle-class Jews feel more comfortable about their lives,” he recalled. But later, again to his surprise, Rosen found that he really liked working with congregants.

Over coffee about 2 miles from his synagogue at Sol Café, in the Chicago neighborhood of Rogers Park — the cafe’s slogan is, aptly, “Coffee that feeds your soul” — Rosen mused on the irony of his current profile as a top activist with a group condemned by the ADL. Among other things, he related, his wife, Hallie Rosen, worked for the ADL for 15 years. This included a stint as associate director of the ADL’s Philadelphia regional office.

Rosen recalled showing his wife the Gaza post, which he believed could well derail his rabbinic career, before uploading it. Always supportive and a fellow traveler on his Israel journey, she told him it was his call.

“I was not sure that I could remain a congregational rabbi at all when I started going in this direction,” Rosen said. “I found, very much to my relief and delight, that I had a congregation that was able to have a rabbi like me doing this stuff even if there were many members of my congregation who didn’t agree with me, and many who were actually deeply pained by the things I was saying and doing.”

Rosen understands the reason that some congregants felt he wasn’t the rabbi they hired. A “small number” left the synagogue, he said, but in his opinion, “they already had one foot out the door.”

An October 2013 report from the Jewish Council for Public Affairs underlines how unusual Rosen’s profile is. Of 552 rabbis from varied points on the political spectrum that the council polled, nearly 40% said they sometimes or often avoided expressing their true feelings about Israel.

Rosen said the report’s findings were consistent with his own observations regarding his colleagues. “Most rabbis just don’t engage in Israel at all. They don’t fit in the AIPAC route,” he said, referring to the American Israel Public Affairs Committee, the powerful mainstream pro-Israel lobby. “But they’re also afraid to speak their truth on this issue…. I confess I was like that for a long time.”

Rosen’s credo for his own congregational leadership is a famous journalistic motto: to “comfort the afflicted and afflict the comfortable.” If he had not become a rabbi, Rosen said, his longtime dream had been to become a newspaper columnist.

But many of those whom he has afflicted don’t think Rosen is doing God’s work. Asked if he had ever worked with Rosen, William Daroff, senior vice president for public policy and director of the Washington office of the Jewish Federations of North America, said, “Thankfully, I’ve never met him.” He called Jewish Voice for Peace “a scourge — anti-Zionist and supportive of policies that will lead to less peace.”

Deborah Lauter, the Anti-Defamation League’s director of civil rights, called JVP the country’s “largest Jewish anti-Zionist organization” and said, through a spokesman, that the rabbinical council Rosen co-chairs “tries to hekhsher” — to bestow kosher certification on — “the anti-Israel movement by claiming that Jewish values and Jewish rituals are consistent with anti-Israel advocacy.”

However thick Rosen’s skin, his activism comes with personal costs. It still pains him to have lost congregants after writing his blog post — particularly those whose babies he named, whose children’s bar mitzvahs he led and whose parents he buried.

“I’m there for them at the most powerful times in their lives. And you bond over that,” he said. “I felt like, ‘Really? After all we’ve been through together? It’s one political issue. You’re going to leave over this?!’”

The ramifications of his activism hit even closer to home at his younger son’s bar mitzvah, which occurred the month after he wrote the blog post. “I don’t want you to mention the word ‘Gaza’ once,” his son told him. Rosen admits that he was busy giving public statements on Israel at the time and trying to enlist supporters. “I was shamefully unfocused on the matter at hand,” he said.

Since that time, Rosen has made some effort to accommodate those of his congregants who feel uncomfortable with his Israel advocacy. Among other things, he may be the only American rabbi who doesn’t want people to “over-identify” him with his synagogue. He begins every outside speech he gives by stressing that he is only speaking personally. His official JRC bio emphasizes that his writings aren’t “official or unofficial positions or policies of JRC.” This, he said, was one of his synagogue board’s red lines in the aftermath of his blog post.

Rabbis who are involved with AIPAC never issue disclaimers like his, Rosen observed. “They don’t for a second take pains to say, ‘By the way, when I speak about AIPAC, I’m only speaking for myself,’” he said. “And I know for a fact that that is a source of great pain to many Jews who belong to these congregations.” The lack of transparency “creates the illusion that the Jewish community is in lockstep on these issues.”

Throughout his activism, Rosen has kept in mind the source of his paycheck. “The minute they feel like I care more about Palestinians than I care about them — who are my congregants — that’s the day, I think, I will lose my congregation,” he said.

Rosen also noted that his blog post came after a 10-year tenure at JRC: “If I had done this one year in, I would have been out on my ass.”

Rosen accounts for his congregation’s tolerance in two other ways: Reconstructionism attracts people seeking alternatives to prior, unhappy synagogue experiences, so they are more open-minded, he said; and they’re a self-selective group.

Gwen Macsai, a JRC member for more than a decade, agreed. “I would say that JRC is very, very open-minded,” said Macsai, a radio producer whose credits include NPR’s “All Things Considered” and “Morning Edition.” “I think the people who are of the kind of Israel do-or-die, right-or-wrong kind of philosophy always have a home at JRC. But I think the more time goes by, the more [there is] a kind of self-selecting group that is a little bit more critical.”

Macsai doesn’t read Rosen’s blogs regularly, she said, and wasn’t sure she remembered which was the first controversy that he raised. “I’m someone who largely agrees with the stuff that he talks about,” she said. Other congregants decidedly do not. Lisa Pildes, who joined JRC long before 1998, when Rosen was hired, considers Rosen’s views on Israel to be “anti-Zionist, wrong-headed, poorly thought out [and] dangerous.

“Certainly, there are times when I wonder why we are still members,” she said.

The synagogue is more than its rabbi, in Pildes’ mind, and she has decades-long friendships with other members.

“There is a community here, which Brant had very little to do with creating and which we are loath to abandon,” she said. “Plus, to put it bluntly, if we and those who feel like we do quit, we would leave Brant with a bigger platform, and there would be no one left in the JRC community to counterbalance his views on Israel.”

Other congregants are more comfortable with a rabbi whose Facebook profile cover photo is a picture he took of a vaulted ceiling at a mosque in Esfahan, Iran, during a 2008 trip. Over coffee at Starbucks in 2011, Rosen told one congregant that he intended to take vacation days to fulfill a dream of participating in an olive harvest at a Palestinian village in the Israeli-occupied West Bank. She told him that if he was serious about taking the congregation on his journey, he had to do so literally.

On the trip, Rosen took congregants to the Deheishe refugee camp, just outside Jerusalem — where they stayed in people’s homes — and to the West Bank Palestinian town of Jenin. They also saw up close the barrier that Israel has constructed to separate its population from the West Bank. Israel states that it built the wall for security reasons, but the barrier also juts deep into the occupied territory at points, to encircle exclusively Jewish settlements there, absorbing land and separating Palestinian farmers from their own land at times. The group also attended a nonviolent rally in East Jerusalem.

“We did a lot of stuff that congregants don’t usually do with their rabbis,” Rosen said. “It was the most gratifying moment of my career, because they were willing to go with me.”

But if Rosen has led some of his congregants to new Holy Land territories, there has been a symbiotic balance, he said. In that same busy year, 2008, the synagogue was constructing a new building, and its environmental task force lobbied for a green building. “I didn’t even know what LEED certification was,” Rosen admitted, referring to the U.S. Green Building Council’s protocol for grading the environmental footprint of buildings. Although JRC aimed for Leadership in Energy & Environmental Design gold, its new building — $9 million according to Chicago magazine—did better: platinum. “We are all still blinking our eyes,” Rosen said.

Africa also didn’t occupy a significant position on his radar when Rosen came to Evanston, but he has been to the continent three times with JRC’s global AIDS task force.

Learning from his community and working face to face with people in the real world are a couple of the reasons that Rosen says he wouldn’t choose full-time activism, which he clearly enjoys, over the pulpit.

“I’m a people person, and my day-to-day work is with people, and that’s what I love about my work,” he said. “I think I would lose that if I became an executive director of a solidarity organization.”